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Synthetic method of compound 2-cyclopropyl-1-(2-fluorophenyl)-2-carbonyl ethyl p-methylbenzensulfonate

A p-toluenesulfonate ester and synthetic method technology, applied in the preparation of sulfonate ester, organic chemistry, etc., can solve the problems of high toxicity, large environmental pollution, and low yield, and achieve short reaction cycle, environmental friendliness, and low toxicity Effect

Inactive Publication Date: 2011-11-16
NORTHWEST NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0026] The raw material price of this method is relatively expensive and the toxicity is relatively high, the environmental pollution is relatively large, the labor protection is relatively large, and the yield is not high, so this method is not suitable for industrialization Production

Method used

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  • Synthetic method of compound 2-cyclopropyl-1-(2-fluorophenyl)-2-carbonyl ethyl p-methylbenzensulfonate
  • Synthetic method of compound 2-cyclopropyl-1-(2-fluorophenyl)-2-carbonyl ethyl p-methylbenzensulfonate
  • Synthetic method of compound 2-cyclopropyl-1-(2-fluorophenyl)-2-carbonyl ethyl p-methylbenzensulfonate

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Embodiment Construction

[0074] The method for synthesizing 2-cyclopropyl-1-(2-fluorophenyl)-2-carbonylethyl p-toluenesulfonate of the present invention will be described in detail below through specific experimental examples.

[0075] (1) Synthesis of o-fluoromandelic acid

[0076] Accurately weigh o-fluorobenzaldehyde (0.01mol, 1.24g), tetrabutylammonium bromide (0.0006mol, 0.19g) and put them into a three-necked flask equipped with 20mL of chloroform (both solvent and reactant) and a thermometer, Mix well and stir at 60°C for 15min. Then add 5.6g (mass concentration 40%) sodium hydroxide aqueous solution drop by drop from the dropping funnel to react, and keep stirring. After the addition, the temperature was maintained at 60°C to continue the reaction for 60 hours. After the reaction was completed, 100 mL of water was added to dilute and the reaction liquid was cooled to room temperature, and the lower layer of chloroform was separated. The aqueous phase was adjusted to pH 1 with 3mol / L hydroch...

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Abstract

The invention discloses a synthetic method of a medicinal prasugrel intermediate, i.e., compound 2-cyclopropyl-1-(2-fluorophenyl)-2-carbonyl ethyl p-methylbenzensulfonate, belonging to the technical field of chemical synthesis. The method comprises the following steps of: making o-fluorobenzaldehyde serving as an initial raw material with chloroform and sodium hydroxide to obtain o-fluoromandelicacid; esterifying, protecting with methoxyl chloromethane and hydrolyzing to obtain 2-(2-fluorophenyl)-2-( methoxyl) acetic acid; performing amidation, Grignard reaction and deprotection to obtain 1-cyclopropyl-1-(2-fluorophenyl)-2-hydroxyacetophenone serving as a key intermediate; and making the 1-cyclopropyl-1-(2-fluorophenyl)-2-hydroxyacetophenone react with paratoluensulfonyl chloride to obtain a target product. The method has the advantages of readily-available raw materials, low cost, high yield, short reaction period, high efficiency, low pollutant emission and environmental friendliness.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and relates to a method for preparing an intermediate of a synthetic drug prasugrel, in particular to a compound 2-cyclopropyl-1-(2-fluorophenyl)-2-carbonylethyl-p-toluenesulfonate Method for the synthesis of acid esters. Background technique [0002] The chemical name of prasugrel is 2-acetoxy-5-(α-cyclopropylcarbonyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine, which is An oral antiplatelet drug jointly developed by Sankyo Company of Japan and Eli Lilly Company of the United States, and was approved for marketing by the US Food and Drug Administration (FDA) on July 10, 2009. This drug is mainly used for patients receiving angioplasty to reduce the risk of heart attack caused by postoperative thrombosis; it is also used for anti-platelet therapy, which can greatly reduce the incidence of myocardial infarction in patients with acute coronary syndrome. [0003] The chemical structur...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C309/73C07C303/28
Inventor 黄丹凤龙玺国胡雨来徐长明牛腾
Owner NORTHWEST NORMAL UNIVERSITY
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